1: H2 / Pd-CaCO3 / ethanol / 76000 Torr / Ambient temperature 2: (i) NaH, THF, (ii) Al-Hg, aq. THF 3: (i) NaH, THF, (ii) /BRN= 635835/ 4: H2 / Pd-CaCO3 / ethanol / 76000 Torr / Ambient temperature 5: (i) NaH, THF, (ii) Al-Hg, aq. THF 6: (i) NaH, DMF, (ii) /BRN= 1722657/ 7: H2 / Pd-CaCO3 / ethanol / 76000 Torr / Ambient temperature 8: (i) NaH, THF, (ii) Al-Hg, aq. THF View Scheme

1: H2 / Pd-CaCO3 / ethanol / 76000 Torr / Ambient temperature 2: (i) NaH, THF, (ii) Al-Hg, aq. THF View Scheme

1: H2 / Pd-CaCO3 / ethanol / 76000 Torr / Ambient temperature 2: (i) NaH, THF, (ii) Al-Hg, aq. THF 3: (i) NaH, THF, (ii) /BRN= 635835/ 4: H2 / Pd-CaCO3 / ethanol / 76000 Torr / Ambient temperature 5: (i) NaH, THF, (ii) Al-Hg, aq. THF 6: (i) NaH, DMF, (ii) /BRN= 1722657/ 7: H2 / Pd-CaCO3 / ethanol / 76000 Torr / Ambient temperature 8: (i) NaH, THF, (ii) Al-Hg, aq. THF 9: (i) NaH, THF, (ii) /BRN= 1724987/ 10: LiAlH4 / diethyl ether View Scheme

hydrogen; Lindlar's catalyst in ethanol P=76000 Torr; Ambient temperature;

potassium carbonate in dichloromethane T=40°C; Wittig reaction; 24 h; Inert atmosphere; optical yield given as percent dediastereoselective reaction;

potassium carbonate in dichloromethane T=40°C; Wittig reaction; 16 h; Inert atmosphere; optical yield given as percent dediastereoselective reaction;

Pd0(tris(tert-butyl)phosphine)2; water; sodium carbonate in toluene T=50°C; 12 h; Inert atmosphere;

1,8-diazabicyclo[5.4.0]undec-7-ene in tetrahydrofuran 18 h; Ambient temperature;

sodium hydride 1.) dioxane, 30 min, room temp.; 2.) 3h, room temp.; Yield given. Multistep reaction;

in diethyl ether T=35°C; 12 h;